Carbon–carbon bond formation in the dichlorobis(triphenylphosphine)nickel-catalysed reaction between Grignard reagents and allylic alcohols

1968 ◽  
Vol 0 (24) ◽  
pp. 1604-1605 ◽  
Author(s):  
Claude Chuit ◽  
Hugh Felkin ◽  
Claude Frajerman ◽  
Georges Roussi ◽  
Gérard Swierczewski
Keyword(s):  
Bond Formation ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
Carbon Bond ◽  
Catalysed Reaction ◽  
Carbon Carbon Bond

Titanacyclopropanes as versatile intermediates for carbon-carbon bond formation in reactions with unsaturated compounds

2000 ◽  
Vol 72 (9) ◽  
pp. 1715-1719 ◽  
Author(s):  
O. G. Kulinkovich
Keyword(s):  
Reaction Mechanism ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
Ethylmagnesium Bromide ◽  
Carbon Bond ◽  
Unsaturated Compounds ◽  
Carbon Carbon Bond ◽  
Reaction Proceeds

Dialkoxytitanacyclopropane intermediates [or titanium (II)-olefin complexes] generated in situ from ethylmagnesium bromide and titanium (IV) isopropoxide react with allylic alcohols and allylic ethers to afford SN2' allylic ethylation products. The reaction proceeds with high regioselectivity and with low to high trans-/cis-stereoselectivity. This observation and others suggest a reaction mechanism involving an EtMgBr-initiated formation of titanacyclopentane ate complex 10 from titanacyclopropane-olefin complex 7 as a key step. Based on this assumption, a modified mechanism of titanium-mediated cyclopropanation of esters with Grignard reagents is proposed.

Carbon–Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)–CF3 Bond Cleavage

2019 ◽  
Vol 84 (9) ◽  
pp. 5635-5644 ◽  
Author(s):  
Longzhi Zhu ◽  
Liyuan Le ◽  
Mingpan Yan ◽  
Chak-Tong Au ◽  
Renhua Qiu ◽  
...  
Keyword(s):  
Bond Cleavage ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Carbon Bond ◽  
Carbon Carbon Bond

Regioselective Carbon-Carbon Bond Formation in Titanium Mediated Reaction of Ethylmagnesium Bromide with Allylic Alcohols and Allylic Ethers

Synlett ◽  
2001 ◽  
Vol 2001 (01) ◽  
pp. 0049-0052 ◽  
Author(s):  
Oleg G. Kulinkovich ◽  
Oleg L. Epstein ◽  
Vladimir E. Isakov ◽  
Ekaterina A. Khmel'nitskaya
Keyword(s):  
Bond Formation ◽  
Allylic Alcohols ◽  
Ethylmagnesium Bromide ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Allylic Ethers

Carbon-Carbon Bond Formation: Palladium-Catalyzed Oxidative Cross-Coupling of N-Tosylhydrazones with Allylic Alcohols

2012 ◽  
Vol 18 (34) ◽  
pp. 10497-10500 ◽  
Author(s):  
Huoji Chen ◽  
Li Huang ◽  
Wei Fu ◽  
Xiaohang Liu ◽  
Huanfeng Jiang
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Allylic Alcohols ◽  
Carbon Bond ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed

scholarly journals Beckmann Fragmentation and Successive Carbon–Carbon Bond Formation Using Grignard Reagents via Phosphonium Salt Intermediates

2016 ◽  
Vol 64 (7) ◽  
pp. 718-722 ◽  
Author(s):  
Hiromichi Fujioka ◽  
Nao Matsumoto ◽  
Yuichi Kuboki ◽  
Hidenobu Mitsukane ◽  
Reiya Ohta ◽  
...  
Keyword(s):  
Phosphonium Salt ◽  
Bond Formation ◽  
Grignard Reagents ◽  
Carbon Bond ◽  
Carbon Carbon Bond
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